Florida No More: A Canadian Snowbird's Plan B (2026–27 Edition)

For years, Florida was the easy answer for Canadian snowbirds. Now the dollar doesn’t stretch as far, insurance keeps climbing, and Canadians staying in the U.S. 30 days or more have to register with U.S. immigration. This guide is a practical Plan B: what to sort out at home, four honest options and a plan for your first winter.

“It saves a LOT of time and research for anyone who is interested in this topic.” — Stephanie, British Columbia

What’s inside

• A Top 10 page if you’re short on time
• Travel medical insurance: what to check before you buy
• Health plan days-away rules, with Ontario in detail and links for every province
• Prescriptions, taxes, pensions and other ties back home
• Mexico, Belize, Costa Rica and the Dominican Republic compared: stays, costs, healthcare, flights
• Quick picks, how to choose and how to avoid rental scams
• Sidebars on Cayman, Panama and why Cuba is off the table this year
• A month-by-month first-winter plan, money tips and two one-page printable checklists

Who it’s for

Average-budget couples, retired or semi-retired, who used to winter in Florida or Arizona and want a modest furnished rental, not a villa. Cuba regulars looking for a new spot will find it useful too. It isn’t for people moving abroad for good or working while away.

About the author

Paul Snozyk runs Cyberco out of Kingston, Ontario. A chef by trade, he has lived in Belize and the Cayman Islands and spent time in Mexico, including one memorable visit to a Mexican hospital. He wrote the guide he wishes he’d had.

Questions

Is this only for Ontario?

No. The Ontario section is the most detailed because that’s where I live. Everything else applies to Canadians from any province, and the “Not from Ontario?” section has official links for every province and territory.

Is it a printed book?

No. It’s a 30-page PDF that you download right after you buy. You can read it on a computer, tablet or phone, or print it at home.

What if rules change after I buy?

If major rules change this season, I’ll update the guide. Payhip lets you re-download the latest version at no extra cost.